Sodium Hydroxide → 6-Cyclopropyl-1-isopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522445Notes

Reaction equation

HRID 1522445 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:17]([O:19]CC)=[O:18])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]([CH3:16])[CH3:15])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C:17]([OH:19])=[O:18])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([CH:14]([CH3:16])[CH3:15])[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67124269Ethyl 6-cyclopropyl-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 71745476-Cyclopropyl-1-isopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 6-cyclopropyl-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (200 mg, 0.696 mmol) in ethanol (5 mL) was added sodium hydroxide (2.088 mL, 2.088 mmol), and the mixture stirred at room temperature for 30 min. The reaction mixture was concentrated in vacuo. The residue was diluted with water (30 mL) and then acidified with acetic acid. The contents were extracted with DCM (3×30 mL). The combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The final product was obtained as 0.17 g (94%). LCMS E-S (M+H)=260.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97-1.12 (m, 4 H) 1.44 (d, J=6.57 Hz, 6 H) 2.27-2.38 (m, 1 H) 2.55 (s, 3 H) 5.07 (quin, J=6.69 Hz, 1 H) 7.43 (s, 1 H) 13.30-14.08 (m, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with water (30 mL)
  3. extractionThe contents were extracted with DCM (3×30 mL)
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f18a3dec2f1417d9e54a34f71ae8ad8
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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